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Workaholic Mike Flaherty is the Deputy Mayor of New York City, serving as Mayor Randall Winston's key strategist and much-needed handler. Mike runs the city with the help of his oddball staff: an anxious and insecure press secretary; a sexist, boorish chief of staff; an impeccably groomed gay activist running minority affairs; a sharp and efficient, man-crazy accountant; and an idealistic young speechwriter. Like Mike, they are all professionally capable but personally challenged.
Themes
Episodes
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- E1 PilotNext upSep 17, 1996 · 22 min
Synopsis

Michael Flaherty and his team grapple with a garbage strike and a political gaffe by the Mayor who accidentally insults gays. In addition, Ashley questions Mike's commitment to their relationship when is nervous about moving in together.
Guest stars: Victoria Dillard (Janelle Cooper), Taylor Stanley (Karen)
- E2 The Great PretenderSep 24, 1996 · 22 min
Synopsis

When Mike is named Sexiest Man in New York by ""Manhattan"" magazine, he has difficulty living up to the notoriety at home. In the meantime, the staff must deal with Mayor Winston's problematic wife during an important dinner.
Guest stars: Deborah Rush (Helen), Robert Trumbull (Priest), Jimmy Palumbo (Bartender), Kim Serafin (Lila), Taylor Stanley (Karen), Sylvia Kauders (Roberta)
- E3 The ApartmentOct 1, 1996 · 22 min
Synopsis

Michael and the Mayor work around the clock to negotiate an end to the garbage strike, which leaves Stuart in charge of the office, to everyone's dismay. And, though they just moved into a new apartment, life is so hectic that Ashley and Michael never get to see each other.
Guest stars: Victoria Dillard (Janelle Cooper), Michael Goldfinger (First Union Guy), Sam Stern (Second Union Guy), Eric Slovin (Man In Hallway), John Scurti (Reporter), Avery Glymph (Reporter)
- E4 Pride and PrejudiceOct 8, 1996 · 22 min
Synopsis

Michael allows a TV crew into the office for a profile on himself, and one of his quotes lands him in hot water with Ashley. In the meantime, Carter goes behind Michael's back to get the Mayor to green-light a controversial project.
Guest stars: Victoria Dillard (Janelle Cooper), Gretchen Mol (Gwen), Taylor Stanley (Karen), Rudy Ruggiero (Journalist), John Scurti (Reporter)
- E5 The RivalsOct 15, 1996 · 22 min
Synopsis

The former Mayor of New York is a constant critic of the current administration, and a plan to appease him has tragic consequences. Meanwhile, Michael and Ashley try to avoid their annoying new neighbors. And Nikki holds a contest among the men in the office to prove that none of them could ever be fathers.
Guest stars: Bray Poor (Yale), Welker White (Maria), Edmund Ikeda (Mr. Fong), Mario Mendoza (Jesus), Tom Lacy (Mayor Garfield), John Harrington Bland (Reporter), Avery Glymph (Reporter), Amy Hohn (Reporter)
- E6 A Star is BornOct 22, 1996 · 22 min
Synopsis

When Mayor Winston's nominee for the Public Schools Chancellor proves an embarrassment to the administration, James urges Mike to stick with the controversial candidate. In the meantime, Ashley considers a career in television on a roundtable show.
Guest stars: Victoria Dillard (Janelle Cooper), John Bedford Lloyd (Dr. Bronsteen), Bill Boggs (Talk Show Moderator), Sylvia Kauders (Roberta), John Harrington Bland (Reporter), Lisa Louise Langford (Reporter)
- E7 Grand IllusionOct 29, 1996 · 22 min
Synopsis

Carter and Nikki plan a fake wedding to make a point about the mayor's stance on same-sex marriages. Meanwhile, Paul is a transformed man when the eye patch he wears after a minor injury gives him unprecedented self-confidence and sex appeal. And an unsatisfied Ashley considers leaving her new TV show for the newspaper again.
Guest stars: Victoria Dillard (Janelle Cooper), William Bogert (Priest), Jane Cecil (Marge), Claudia Rocafort (Beautiful Woman), Taylor Stanley (Karen)
- E8 The High and the MightyNov 12, 1996 · 22 min
Synopsis

Michael needs a favor from famed real estate developer Dan Donaldson, but the price Mike has to pay may not be worth it. In the meantime, Paul finds it hard to crow about the city's lowered crime rate, since he's just become a victim of a robbery-again. And Mike and Ashley can't agree on what show to watch when they're in bed.
Guest stars: George Wendt (Dan Donaldson), Andy Daly (Payroll Guy), Taylor Stanley (Karen)
- E9 Meet Tommy DuganNov 19, 1996 · 22 min
Synopsis

An opinionated school janitor becomes "Mayor for a Day" when he wins an essay contest intended for schoolchildren. Meanwhile, the Mayor wants to change his image.
Guest stars: Woody Harrelson (Tommy Dugan), John Harrington Bland (Reporter), David Carlson (Reporter), Lisa Louise Langford (Reporter)
- E10 The CompetitionNov 26, 1996 · 22 min
Synopsis

When the Mayor's office competes against City Council in an annual Thanksgiving contest, the stakes are high, since the losers must croon a show tune in front of the press. James has trouble breaking up with a longtime girlfriend visiting from Wisconsin.
Guest stars: Victoria Dillard (Janelle Cooper), Ed Koch (Ed Koch - The Judge), J. Smith-Cameron (Lisa), Stephen Colbert (Frank), Jennifer Garner (Becky), Brian Tarantina (First Homeless Man), John Sobestanovich (Second Homeless Man), William Preston (Older Homeless Man)
- E11 Dog Day AfternoonDec 10, 1996 · 22 min
Synopsis

Mike tries to appease the disgruntled Police Commissioner by honoring a beloved police dog who has recently died. But things go awry on the way to the funeral when Paul and Carter lose the canine's body. And Mike buys an air hockey table for the staff proving Stuart a very big talker.
Guest stars: Victoria Dillard (Janelle Cooper), Jerry Adler (Police Commissioner), Jason Antoon (Cab Driver), Robert Maschio (Bingo's Partner), Taylor Stanley (Karen)
- E12 Criss CrossDec 17, 1996 · 22 min
Synopsis

Michael substitutes for the Mayor on a political talk show, facing off against Ashley on a hot-button issue. Meanwhile, Paul plays City Hall Santa while battling a terrible bout of the flu that is sweeping the office. And everyone finds themselves going to Carter for romantic advice.
Guest stars: James Murtaugh, Paul Reggio (Bartender), Taylor Stanley (Karen), John Scurti (Reporter)
- E13 Bye Bye LoveJan 7, 1997 · 22 min
Synopsis

The office rallies to lift Mike's spirits after his break-up with Ashley, but he resists their best efforts. That is, until he decides he needs a friend and reaches out to Nikki in the middle of her date with the perfect man. And Paul sets a New Year's resolution to be less gullible.
Guest stars: Ken Marino (Dan), Tom Riis Farrell (UPS Guy), Eric Kushnick (Pizza Guy), Sylvia Kauders (Roberta)
- E14 Starting OverJan 14, 1997 · 22 min
Synopsis

Michael is uncomfortable with his newly single status when he realizes he's actually on a date with new assistant district attorney Danielle Brinkman. Meantime, Paul meets the president of his fan club, Claudia Sacks, who has arranged the group's first meeting. And Carter and Stuart have a little too much to drink and end up in an awkward situation.
Guest stars: Victoria Dillard (Janelle Cooper), Iraida Polanco (Cleaning Lady), Judy Stadt (Waitress), Courtney Thorne-Smith (Danielle Brinkman), Faith Prince (Claudia Sachs)
- E15 Gabby's SongJan 28, 1997 · 22 min
Synopsis

Mike butts heads with a hard-nosed new chief of staff appointee, Gabby Sanchez, who is unmoved by his best efforts to win her over. Meanwhile, Paul ponders taking his relationship with Claudia to the next level.
Guest stars: Constance Marie (Gabby), Taylor Stanley (Karen), Jared Johansen (George), Tom Shillue (Man in Hall), Faith Prince (Claudia Sachs)
- E16 Kiss Me, StupidFeb 11, 1997 · 22 min
Synopsis

It's Valentine's Day, and Carter's old flame Spence wants to meet with him. Meantime, Mike goes on a date from hell with a beautiful friend of Nikki's, and Paul's romantic evening with Claudia becomes unforgettable for all the wrong reasons.
Guest stars: Luke Perry (Spence Kaymer), Kim Dickens (Veronica), Anney Giobbe (Melissa), Faith Prince (Claudia Sachs)
- E17 An Affair to RememberFeb 18, 1997 · 22 min
Synopsis

For the Mayor's 50th birthday, Paul is determined to get his ""old friend"" George Stephanopoulos to attend the event; as Michael arranges for birthday wishes from David Letterman, Patrick Ewing, Al Michaels, Dan Dierdorf, Frank Gifford, Rosie O'Donnell, Larry King, and the cast of Rent. But in the midst of the planning, a scandal swirls about the Mayor's presumed affair with a staffer from the Governor's office.
Guest stars: Deborah Rush (Helen), George Stephanopoulos (George Stephanopoulos), Anne Twomey (Holly), Dan Dierdorf (Dan Dierdorf), Frank Gifford (Frank Gifford), Wilson Jermaine Heredia (Wilson Jermaine Heredia), Larry King (Larry King), David Letterman (David Letterman)
- E18 SnowboundFeb 25, 1997 · 22 min
Synopsis

A major snowstorm hits Manhattan, causing a chain reaction of mishaps at City Hall. Mike desperately tries to meet his longtime crush on her last night in the city; Paul accidentally offends the Mayor on the radio; Carter and Stuart are locked in the boiler room; and a nudist is on the loose in the Mayor's office.
Guest stars: Victoria Dillard (Janelle Cooper), Amanda Peet (Shelly), Gabriel Macht (Naked Guy), Faith Prince (Claudia Sachs)
- E19 StripteaseMar 4, 1997 · 22 min
Synopsis

Michael discovers that his new girlfriend, Gayley, is paying for law school by moonlighting as a stripper. Meantime, Claudia catches Paul in a lie, and Nikki plays mind games with Stuart.
Guest stars: Victoria Dillard (Janelle Cooper), Cynthia Watros (Gayley), Stephen Scibetta (Strip Club DJ (uncredited)), Sylvia Kauders (Roberta), Faith Prince (Claudia Sachs), John Harrington Bland (Reporter), Marie Gabrielle (Reporter), Jordan H. Fischer (Reporter)
- E20 Deaf Becomes HerMar 18, 1997 · 22 min
Synopsis

It's damage control time when the Mayor's inept new sign-language interpreter inadvertently offends the deaf community, and Michael rushes to appease one of its leaders, Sarah Edelman. Meantime, Paul is worried that Claudia wants to move in permanently.
Guest stars: Victoria Dillard (Janelle Cooper), Marlee Matlin (Sarah), Sam Seder (Bogus Temp), Lewis Merkin (Tim), Carole Addabbo (First Dinner Guest), Frank Dattolo (Second Dinner Guest), Faith Prince (Claudia Sachs), David Carlson (Reporter)
- E21 Hot in the CityApr 1, 1997 · 22 min
Synopsis

On the personal front, Mike struggles with his ex-girlfriend, Carrie, who is desperate to bear his child (with or without his participation). At the office, he's playing peacemaker after the mayor's ill-chosen words split up a beloved band just before their reunion concert.
Guest stars: Victoria Dillard (Janelle Cooper), J.K. Simmons (Kevin), Charle Landry (Tommy), Kathleen Chalfant (Mother Superior), Steve Gaasche (Band P.A.), Daphne Zuniga (Carrie)
- E22 Bone FreeApr 29, 1997 · 22 min
Synopsis

The men in the office find love-or rather, lust-is in the air, causing more than a few problems. And Nikki wonders whether her new heartthrob, George, is a struggling writer or an untalented mooch.
Guest stars: Victoria Dillard (Janelle Cooper), Sam Seder (George), Anna Holbrook (Heidi Longley), Rebecca Boyd (Dr. Barrow), Ellen Bethea (Reporter)
- E23 The Mayor Who Came to DinnerMay 6, 1997 · 22 min
Synopsis

The Mayor separates from his wife and moves in with Michael, much to Mike's chagrin. Meanwhile, designer Isaac Mizrahi helps the Mayor's office with a charity fashion show and gives Nikki a once-in-a-lifetime chance to strut the runway in one of his creations.
Guest stars: Victoria Dillard (Janelle Cooper), Deborah Rush (Helen), Isaac Mizrahi (Isaac Mizrahi), Rachel York (Beautiful Woman), Kathleen Claypool (Mrs. Schnoll)
- E24 Mayor Over MiamiMay 13, 1997 · 22 min
Synopsis

Despondent over his separation with his wife, the Mayor decides on a whim to take a road trip with Paul, leaving Mike in charge of New York City and scrambling to find out where they went.
Guest stars: Victoria Dillard (Janelle Cooper), Marin Hinkle (Carolyn), Marcia DeBonis (Ticket Agent), Timothi-Jane Graham (Waitress), Faith Prince (Claudia Sachs), John Harrington Bland (Reporter), Marie Gabrielle (Reporter), Christopher J. Marcinko (Reporter)
Cast & crew
Created by Gary David Goldberg, Bill Lawrence
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Charlie Sheen
Heather Locklear
Barry Bostwick
Richard Kind
Alan Ruck
Michael Boatman
















